


I've got to break away (so take my hand now)

by sarcastic_fina



Category: The Vampire Diaries (TV)
Genre: All Human, Alternate Universe - Assassins & Hitmen, Complicated Relationships, Depression, Explicit Language, F/M, Grief/Mourning, Man all of these tags are sad but i swear it has a happy future, Moving On, Past Alcohol Abuse/Alcoholism, Past Child Abuse, Past Domestic Violence, Past Dysfunctional Relationships, Sexual Content, Stalking, Violence, dark themes, past suicide attempts
Language: English
Status: Completed
Published: 2015-05-08
Updated: 2015-05-08
Packaged: 2018-03-29 14:32:54
Rating: Mature
Warnings: Graphic Depictions Of Violence
Chapters: 1
Words: 9,272
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3899794
Author URL: https://archiveofourown.org/users/sarcastic_fina/pseuds/sarcastic_fina
Summary: <blockquote class="userstuff">
              <p>(<b>AH/AU</b>) Damon Salvatore wouldn't exactly say he loves his job. Maybe once upon a time he did, but things have changed recently. Still, he does what he's paid to. A hitman for hire, he's never flinched on the job before, not until Bonnie Bennett's file ends up in his hands, and then he finds himself falling for his mark. What's an assassin to do?</p>
            </blockquote>





	I've got to break away (so take my hand now)

**Author's Note:**

> **polyvore** : [Bonnie](http://www.polyvore.com/bonnie_assassin_au/set?id=157906089)

If anybody asked, he had a perfectly believable origin story for why he became an assassin. It was chock full of betrayal and death and a poor-me-my-daddy-didn't-love-me undercurrent equipped with on-going abandonment issues, free of charge. Of course, nobody ever asked him  _why_ , they were usually too dead for that. But Damon liked to cover all his bases. Hence, when he was bored, he would mentally pen out his 'this is why I am who I am, deal with it' villain speech. Just on the off chance anyone  _did_  ask him.

See, it all started when he was eight years old, and his father told him that he was too weak-willed to be his son. The implication, obviously, was that Damon was not his father's son at all, but someone else's. But the reality was simply that his father didn't love him; not who he was or what he had to offer, which, admittedly wasn't much at only eight.

Giuseppe Salvatore was a mean bastard who took every opportunity to demean his wife and children, especially when he had a few drinks in him. Suffice it to say, that was often. Anyway, so Giuseppe told Damon that he was weak and pathetic and he would never amount to anything, words Damon held close to him all through adolescence. Of course, unlike his brother, who went the route of trying to prove Giuseppe wrong, Damon went the other direction, by taking every opportunity offered to him to do the wrong thing.

Date his father's business partner's sweet, innocent daughter and then break her heart? Check. Actually, double check. Although he would argue that Katherine was just as rebellious as he was, and far from innocent, her twin sister Elena was definitely the cry-into-her-pillow type, especially after walking in on him on his knees, servicing her sister the day after their three month anniversary. Did he mention he was an ass…? Maybe it was just implied.

Totalled his dad's two favorite cars? Check and check.

Academic suspension for skipping? Check.

Admitted to the hospital for alcohol poisoning? Check times three.

Became familiar with the local law enforcement? Super check.

Dropped out of college? Huge check.

So, clearly, Damon was on a path set for destruction. But, he would like it listed on the record that it was his dad's fault.

When Damon was twelve years old, he lost his mother. Lily was kind; sweet, gentle, and  _endlessly_  loving. How she got herself tied to Giuseppe for all her life, Damon would never know. She used to tell him, as she rubbed his back while he cried in her lap over his father's latest act of 'discipline,' that he was a good man once, and she hoped one day he would be again. Damon thought her memory was probably wrong; that, or she wanted desperately to hold onto false hope to make her current situation seem better.

According to the police, Lily Salvatore tripped on the stairs. An unfortunate accident. Damon knew different. She'd had a suitcase in hand, her fingers tightly coiled around the handle. Stefan, four years old at the time, was already in the car seat, but Damon had wanted to wait for his mother, worried that his father would wake up from his late afternoon nap (read: he passed out from drinking too much and Lily turned him on his side so he wouldn't choke on his own vomit).

They were leaving, for good, his mother had promised. She had a friend, Sheila, who she'd met while she was taking a few college courses in secret. Sheila was a professor and had noticed the bruises Lily often tried to hide. She'd offered, countless times, to help her in any way she could. Damon overheard them sometimes, talking in the kitchen—"You just say the word, Lily, I'll put that husband of yours down for good," Sheila promised—Damon always hoped his mother would take her up on the offer. So that was it, freedom was on the horizon.

Lily got down three stairs before Giuseppe's hand was coiled in her hair, yanking her backwards. She let out a fearful shriek and her suitcase toppled down the stairs, making a loud banging noise with each step that it hit before spilling across the floor as it reached the bottom.

Damon lurched forward, wanting to help, but Lily raised her hand to stop him, worried he too might get hurt.

He listened. And he would regret that for the rest of his life.

What his father said came to him later in pieces, fractured words that would haunt his worst nightmares.

"You think you can just leave me? Take my sons and walk away, huh? I put a roof over your head, I kept you fed, I called those pathetic little boys of yours my own, and you want to walk away? You don't get to do that. Not to me. This is my home, and you are  _my_ wife. Do you understand me?"

"Giuseppe, please, please, you're hurting me. Just let us go. We'll never bother you again,  _please_."

"You want to leave so bad,  _huh?_  Here then, let me help you."

Damon would never forget the sound of her scream as she fell, nor he would forget the way her body hit the floor at his feet, her arms at a funny angle and her head turned in a terrifyingly  _wrong_ way. He knew, without having to check, that she was gone, and she was never coming back.

He stood there, in the foyer of his childhood home, as his father walked right past him and out the door. Giuseppe gathered Stefan from the car and put him in his bedroom. He gathered up the suitcase and put all of Lily's clothes back where they went. He took the bags from the trunk and did the same with Damon's and Stefan's. And then, with a truly Oscar-worthy performance, he called the police, sobbing, telling some ridiculous story of how his wife had slipped on the stairs and he was so  _scared_. She wasn't breathing and her neck looked like it was broken, what should he do?! Later, Damon would vomit, heaving up the contents of his stomach as he remembered how easy it had been for his father, as if he'd planned it, even practiced it in the mirror.

When the ambulance arrived, they pulled Damon off to the side, asking him if he was okay, if he could tell them his name and what happened. His father squeezed his shoulder so hard, it would bruise later. Damon never said a word; they chocked it up to shock.

He would wonder later if his father paid everyone off to put it down as an accidental death, or if they truly were so terrible at their jobs that they never suspected or noticed anything out of order. Regardless, Lily Salvatore was seen as an unfortunate loss, an accident that could have happened to anyone. Damon kept his silence, and with it, his fate.

By the time he was nineteen, he had two suicide attempts under his belt. He didn't trash his father's cars for nothing, obviously. Oh, it was considered adolescent mischief. He was drinking and he had a terrible record for never following the rules. But in all honesty, he was fourteen when he drove the first car into a pole and he hoped he didn't walk away from it. The second time, he was nineteen, and he drove through three red lights before he was t-boned by a family van and spent a good two weeks in a coma. When he woke up, it was to the brooding eyes of his eleven-year-old brother leaning over him; exhausted, rumpled and beyond angry.

"Don't ever do that again," Stefan gritted out.

"C'mon, you didn't even like that car," Damon dismissed. "It was flashy, and ugly. Totally waste of cash."

"This isn't about the  _car_ , Damon. You think you're the only one who lost a mom? The only one who has to put up with our dad?" He shook his head, his eyes filling with tears. "Without you, I'm the only one left. Do you get that? If I lose you, I'm  _alone_. So just…  _don't_. Okay? Because I can't lose you too."

Damon stared at him a long moment, every inch of his body aching, but worse than all of that was seeing his brother hurt and disappointed because of  _him_. So he nodded. "Okay."

That was the last time he crashed a car. Well, at least for non-work related reasons.

Stefan was thirteen when Damon left. He promised to write and visit and check in on him, but he only managed a few emails and two phone calls before he got himself in some water. Damon had a smart mouth, and he liked playing the odds even when they were nowhere near his favor, which got him into debt with a local bookie. He was living in Chicago at the time, a far cry from small town Mystic Falls, Virginia. To pay off his debt, his bookie offered him a deal. Do a little work for him and he'd scrub it clean. Feeling rather fond of his knee caps, he agreed.

At first, it was just collections.

Growing up, Damon had gotten good at fighting. Shortly after his mom died, he knew something had to change, so he'd started visiting the local gym and he'd taken up boxing. It helped with the aggression, letting him focus all of it on something while exhausting him so he wouldn't take it out on anyone else. By the time he was fourteen, his father stopped pushing him around, recognizing that his prey would finally fight back, and he probably wouldn't win. So by twenty-twenty, Damon was a more than capable fighter, and when push came to shove, he was like a bulldog.

Collections wasn't too hard, he even grew a certain fondness for it. Maybe it was all that built up resentment for his father, but making someone else spill blood felt like a release valve for him. After a while, he wasn't doing it to wipe out his debt anymore, but because he enjoyed it and it paid well. But there was a ladder to those sorts of things, and soon a choice was handed down to him. He could stay small time and local, or he could climb and create a better job and name for himself. Damon decided to climb.

By the time he was thirty-five, he had a reputation for getting the job done; the bloodier, the better. He took pride in his work, striking off each name with the conviction that whatever name crossed his desk deserved it. People that got the attention of his clients weren't often of the good and pure variety, so in a way, he considered it a gift to the outside world that he was ridding it of a few low lifes. That said, he was getting a little tired of the game. His father had died six years earlier – liver failure, what a shocker – and without him still walking the earth, Damon felt his hatred and resentment begin to dwindle. The drive to hurt other people was becoming more of a burden than anything else. He found himself missing home and, more than that, missing his little brother.

But a job was a job, and he wasn't so sure he could come back from the things he'd done. It was better to be the monster he knew he was than play at being anything else.

When Bonnie Bennett's file was dropped in his mailbox, he hadn't given it a second thought. She was a business woman, running her own herbal remedies and holistic shop, and, while she didn't fit with his usual type, she was who he was hired to kill, so he would. As per usual, he spent a few weeks tailing her, trying to get her schedule down so he could find that exact right moment to strike.

As a child, Damon used to people-watch with Lily in the park. She would sit him on a bench, a bag of bread crumbs in her lap to toss to the waiting ducks. "It's a good life lesson," she told him, offering a large piece of bread to her favorite duck, whom she'd named Annabelle. "There's a lot you can learn from observing how other people act, especially when they don't think anyone is looking."

He hadn't had much patience for it then, but he wondered if maybe it had more to do with his father and his inability to understand his motivations. For as long as he could remember, Giuseppe buried himself in a bottle, choosing it over his family, time and time again. Oh, he could play the perfect father and husband when eyes were on them, when they had to go to the many Mystic Falls functions and put on a show of being the perfectly happy family, but behind closed doors he was nothing short of a monster. For that reason, Damon thought that people-watching had little to offer, there were too many unknown factors.

It wasn't until later that he realized just how vital it would be to his job; that knowing schedules and habits, allergies and fears, would make taking out a target all the easier. How quick were they to spook? Did they take a dangerous route to work? Were they allergic to shellfish? He learned everything he could.

Bonnie was a creature of habit.

On Thursdays, she met her best friend Caroline for lunch. A bubbly blonde woman, that he was pretty sure graced his afternoon news as an anchor, greeted Bonnie with a hug every week, shrieking and giggling like she hadn't seen her in ages. She was also at least six months pregnant, which Bonnie seemed pretty excited about since her hand wandered to Caroline's stomach more than Caroline's did. They went to the same restaurant every week, and Bonnie's order rarely varied; chicken club sandwich, a salad, and a strawberry shake. Caroline's order changed every week, except for the fries; she always ordered a side of fries and dipped them into Bonnie's shake. Damon would put money down that they grew up together; he didn't bother looking into Caroline since she only spent one day a week with Bonnie, making it easy to work around their friendship to take out his target.

After lunch, they hit the baby store, where they spent most of their time  _ooh_ ing and  _aww_ ing but never buying. Damon had yet to see the husband, but he saw an expensive ring on Caroline's hand and she frequently mentioned that "he's working another double. I swear, if he's not in scrubs, he's in the nursery, painting and putting the crib together. He's nesting worse than I am."

On Friday and Saturday, Bonnie had a date. Each time a different guy; men that Damon was pretty sure Caroline was setting her up with. She was attractive and could definitely get her own dates, but Caroline had 'matchmaker' written all over her, and Bonnie didn't look half as enthused as he imagined she would if she were going on a date she  _wanted_ to be on. In her defense, he'd looked up every one of them and none of them were worth taking home.

Seymour – seriously, who even named their kid that? – had some serious debt racked up and very,  _very_ poor credit. Chris – or Neckbeard, as Damon mentally called him – had a wife.  _Surprise!_ Martin was a creep; he spent more time staring at her legs than her face. Admittedly, she had a great pair of legs, but seriously, man, learn some manners. Jeremiah wore too much cologne; Damon could smell him across the room and he was pretty sure it was giving Bonnie a headache since she kept rubbing her temple and leaning away from him. Cole had a police record longer than Damon's, which was saying something, considering his youth had been chock full of indiscretion. And finally, Owen wasn't too bad, he used to model for an underwear brand that Damon decided never to use again for  _reasons_ , he had good credit, no secret wives or children, and a steady job. But he had shifty eyes.  _So_. Deal breaker, obviously.

Apparently Bonnie thought so too, because instead of taking any of them up on a second date, she continued her life as previously scheduled. Sunday was her dancing day; she rented out a space and spent her afternoon dancing her shapely ass off, and it was, well... mesmerizing came to mind. All that pent up passion on display, her body bending and moving to a song he couldn't hear from where he was watching her through a scope in a building across the street. If he wasn't an assassin, he'd feel like a perv. Which was worse? Nah, definitely perv.

Sundays were his favorite, if only because he felt like he was seeing a part of her that she usually kept hidden. Under the loose fitting clothes and the polite attitude and the friendly smile she offered to any old stranger than entered her shop. In her dance studio, with her hair falling in her eyes and sweat dripping down her skin, she let loose the animal inside and took it for a spin. She was beautiful. Stunning.  _Intoxicating_.

Mondays were her 'back to business' day. Her hair was back to being carefully coifed, her clothes were pristine and professional, and the only thing she had time for was making sure her customers had the best experience possible in her shop. She made her own candles; a little sign in the window boasted so. He wondered how her apartment smelled, a mixture of different scents and beeswax lingering in the air. He bet she was a honey and vanilla type; every candle and Glade plug-in probably hinted of those earthy scents.

Tuesdays were her yoga days; she closed up shop an hour early and met up with a few friends to do yoga in the park. She was a bendy little thing, but he already knew that from her dancing. When the others left, she would linger, laying on her mat in the shade of a tree, sucking back water from her bottle. He still had no idea why she was being targeted; so far as he could tell, she was average, with no ties to anything questionable.

On Wednesdays, she had book club. She wrote her thoughts down on a notepad, detailing the parts she wanted to discuss and the motivations she guessed for why the characters did what they did. Sometimes he wondered what she would say for him. Would she sympathize or demonize? Would he be the anti-hero or the villain? He decided that, of all the people he had killed in his life, she would be the most likely to ask him  _why_. But instead of being eager to tell his story, he found himself wondering if his reasons had ever been good enough.

Three weeks in, he realized why they wanted her dead. She didn't rent her shop, she owned it, and it was part of a neighborhood that was being torn down so expensive condos could be put up in their place. Bonnie was one of a number of people that were arguing against it, and because she owned her shop and was refusing the payout they were offering to have her removed, they decided it would simply be easier to "shut the bitch up." While Damon had heard of a few jobs like that, it had never been his slice of pie. The people he hit were generally criminals, not average joe's just trying to live their lives. He wasn't sure how he felt about that, as he'd never really had to feel anything when it came to a job.

His bosses were getting antsy, however, so it was time to pull the trigger and get it done with. Damon had killed people a number of different ways. There was the from-afar approach, but he wasn't much for sniping. Guns weren't generally his forte, even if he knew how to use them, having been taught by his first partner, back when he was still in collections. Damon preferred the up close technique; it was probably disturbing, and far too telling of his mental instability, that his go-to was to break a person's neck.

Bonnie had a pretty neck.

He bumped into her on a Friday morning; she was just leaving her favorite grocery store. She had a bag of oranges hanging from her hand and when he knocked into her, it fell to the pavement, splitting open and sending her oranges rolling in different directions.

"Shit, sorry. Here, let me help." He grabbed up three, one nearly gliding into the gutter, while she grabbed up the remaining two.

As she stood, cleaning them off on her skirt, she raised her chin to thank him, before stopping suddenly. She peered up at him, her brow furrowed.

He half-smiled, slightly put off by her reaction. "You got a spare bag for these?" he wondered.

Shaking her head, she smiled suddenly. "Sorry. I… You reminded me of someone for a second. Uh… Bag, right, I…" She pulled her purse open, the handle sliding down her arm. "You can just throw them in here."

He tossed the three oranges inside and then rubbed his hands together absently. "Hope they're not bruised… Do oranges bruise?"

"I don't know." She shook her head. "I can't say I've ever wondered."

"Something to Google later." He looked her over, finding it a little strange to be this close to here when for so long, he had only been seeing her from afar or through his camera lens. "I'm Damon, by the way." He held a hand out for her.

"Oh." She took his hand and gave it a firm shake. "Bonnie."

He nodded slowly. "You live around here, Bonnie?" He shrugged one shoulder. "I'm new to the area. And I think I might be a little lost…"

Her brows hiked. "Anywhere in particular you were looking for?"

"A good restaurant." He smirked then. "And some nice company for dinner, if you're interested."

She let out a little laugh, her cheeks flushed. "Wow, you work fast."

"Is that a bad thing?" he wondered.

"I don't know," she admitted, biting her lip. "I can tell you that Zorro's around the corner makes an amazing pasta."

"I'll take your word for it… Care to see if I agree?"

She stared up at him, searching his eyes. "I don't even know you," she said, as if she were trying to convince herself more than him.

"Then this is a great opportunity to change that."

"You do this often? Just pick up women off the street?"

"Only women who might be carrying bruised oranges because of me. So? What do you say?" He tipped his head curiously. "It's just dinner. You can leave at any time."

Licking her lips, she looked away, giving it some thought, and then raised her chin. "All right. Dinner. But I'm buying my own and… if I go to the bathroom and don't come back, you take the hint."

He laughed under his breath. "It's a pretty big hint, I think I'll catch it." He took a step back then. "Shall we?"

She nodded, and stepped forward, leading the way down the street and around the corner. Zorro's was a well-known and fairly popular Italian restaurant. Damon had ordered out but never eaten in, so he was fairly comfortable thinking they wouldn't recognize him and blow his 'new to town' cover out of the water. They were seated at a table near the window, where Bonnie asked for just a glass of water while he asked for a bottle of their finest red wine.

She raised an eyebrow at him as she reached up to play with her earring absently, a menu open in front of her. "Wine, huh? I thought this was just a casual dinner."

"Wine can be casual."

"Not at how much that bottle's going to cost."

His lips curled up at the corner. "Since we're getting separate bills, you won't have to worry about it."

She shook her head, pursing her lips to hide a smile. "So what do you do then?"

"Ah, straight to the point, I like that." He leaned back in his chair. "I'm a contractor. People tell me what they want and I make it happen."

"That sounds rather vague."

"Vague makes sure I get paid. People are complicated. Sometimes they want services that aren't… usually on the menu. I make that happen."

She stared at him searchingly, resting her elbows on top of the table. "You sound like a gigolo."

He laughed, a deep sound straight from his belly. "Maybe in another life."

She hummed, her eyes narrowed curiously. "So what kind of… services?"

He licked his lips, his eyes wandering over her face. "What would I have to say to get you to share a glass of wine with me?"

"The truth," she said simply.

"Honesty is big with you."

She nodded sharply. "It's a deal breaker."

"Are we on the verge of making a deal, Bonnie?"

"I don't know." She sucked her bottom lip between her teeth. "It's strange… I feel like I know you. Like I've seen you somewhere…"

"There's not much to know. I'm thirty-five, self-employed, I have a nice apartment, no pets, but I've considered a cat a few times. I like music, a lot. I'm a terrible dancer, but it's never stopped me. I prefer bourbon to wine, but you look like a red wine lover. I don't have a lot of friends, curse of my job, but I have a brother. We're…  _estranged_ , but, he's family. Always will be."

He looked up, nodding as a server held the bottle of red wine out for him to see and then poured him a small glass. He smiled when Bonnie allowed the waiter to pour her a glass too. They each put in their order for dinner and then the waiter was gone.

"What about you?" he wondered, before giving his glass a swirl, sniffing the wine briefly, and then taking a sip. "What makes Bonnie tick?"

She took a drink from her glass and then placed it on the table, her fingers teasing along the stem. "I'm an only child, spent most of my time at my Grams' house, always underfoot… I own my shop, a few blocks from here. I have friends, but only one best friend. Caroline." She smiled fondly. "We've known each other since we were four. In… three months, I'll be a godmother to her daughter. Um… let's see, what else… Oh, I was prom queen  _and_ valedictorian… I was a cheerleader in high school, which I  _hated_ , but they cancelled the dance club, so it was my next best option." She nodded, her eyes turned up in thought. "I have no pets, but I'm partial to cats, and that's it. I think."

He briefly considered telling her that wasn't it. That he'd seen her. She chewed on her nails when she was she was worried and large dogs scared her. She tended to enjoy jazz music over pop, unless she was dancing and then all she needed was a quick tempo. Bees freaked her out, but she loved having fresh flowers in her shop from the florist around the corner. She always walked slower in front of bakeries and the smell of fresh bread made her smile. When she was really happy, her cheeks dimpled, and she was terrible at faking a smile.

While some of that was information he would have gathered on any mark, other parts weren't, they were just  _things_. Things he noticed, things he liked, thing that interested him for some reason. When it came to a target, he learned their schedule because it was necessary, not because he was sincerely curious about their life. But Bonnie was different.

"You said you had a brother?" she asked, taking another sip of her wine.

"Uh, yeah, I do. I haven't seen him for…"  _Fourteen years_. "A long time, though. I left when he was still pretty young. He was in middle school and… I don't know. Time got away from me."

"It tends to do that." She sighed, leaning back in her chair. "What about now? Why not contact him? Rebuild bridges."

He smiled briefly, emptily. "I'm pretty sure that ship sailed a long time ago."

"Well, you're a port, so it can always come back around if you want it to."

He peered at her a moment, head tipped thoughtfully. "Maybe."

"Tell me more about your job."

"What do you want to know?"

"I don't know…" She shrugged. "It just sounds… curious. Do you  _enjoy_ it?"

He looked down at the table a moment. "It's…" He frowned. "In the beginning, when I first started, I didn't think I could do it. I was… pretty sure I'd fail. And when I didn't, I thought it said something about me,  _defined_ me, so I went with it. I thought that if I could do it, and do it well, then it must be my calling."

"And was it?"

He raised his eyes to meet hers. "When you find that something that fits you, nothing should be able to shake the foundation of it. It should just be  _solid_ , unquestioned. But a few years back, I started asking myself if it was something I could keep doing… If I even  _wanted_ to. And I don't think I had an answer until a month ago." He leaned forward then, smoothing a hand over the cloth-covered table. "It was staring me in the face. Something obvious. Clarity is a funny thing. You think you have an idea of who you are or what you want and then…  _Bam_. It hits you in the face like a brick."

Humming, Bonnie watched him, trying to put the pieces of the puzzle together. He knew she couldn't though. Who would come to the conclusion that the person sitting across from them was a hired killer? No one.

He was dressed simply, a long-sleeved shirt rolled up to his elbows and a pair of jeans. Both of which likely cost a pretty penny, but he was paid well for his services and he tended to splurge on what he liked. Still, Damon didn't look like an assassin. He didn't carry around a gun wherever he went or offer a sinister smile to give his mark the heebie-jeebies. He was simply a man; handsome and charismatic. He was the devil a beautiful woman flirted with, none the wiser.

"Why'd you leave your brother?" she wondered, throwing him for a loop. "You said he was young, middle school, so you must've been older… College age?"

He nodded. "Twenty one-ish, around there. I failed out of college the year before. Crashed my father's Porsche the year before that."

"Why?"

"Why did I fail or why did I crash the car?"

"Either or. Both. You pick."

He let out a long sigh and sat back, stretching one of his legs out until his foot bumped hers; she let him, choosing not to retract her foot but to let it lean against his. "I wasn't fit for college. I went because it was expected of me, not because I wanted to. But I was trying… To fit in, make amends, be a better brother… Unfortunately, I didn't have it in me to do that." He smirked emptily. "So I stopped going, and eventually they told me I no longer qualified to attend their  _prestigious_  school..." His eyes widened for emphasis.

"Do you regret it?"

He screwed up his mouth, turning his eyes out the window. "Not really. I mean, I have more than a few regrets, but college isn't one of them. I just… wasn't that person."

"So what kind of person are you?"

He narrowed his eyes at her playfully. "You ask a lot of questions for a first date."

"Is that what this is?" She smiled widely, showing off bright, white teeth.

"What did you think it was?"

"An expensive bottle of wine, no strings, good company…" She shrugged, and raised her glass to her lips once more.

"Generally, that is exactly what it would be, but in this case… I might like strings." He crossed his arms and leaned them on the table. "Any more questions?"

"Why'd you crash the car?"

He licked his lips then, and looked down.

Seeming to read his mood, she said, "You don't have to talk about it… I can pick a different topic."

He shook his head, and looked up at her. "I was nineteen. And it was the seven year anniversary of my mother's death. She was… Uh…" He paused, his throat tightening. "Sorry. She…" He tapped his fingers on top of his arm and admitted, "I haven't talked about her in a long time."

Bonnie reached across the table, and laid her hand atop his, stilling his fingers. He stared down at it a long moment. Her skin was warm and smooth, her fingers long, perfect for the piano. He had one at home, though he never played it. It reminded him of his mother, of her daily lessons, telling him to sit up straight and play like she knew he could. He'd been far too impatient to play the piano, but Stefan had excelled at it, much like with most things.

"She was…  _kind_ ," he said quietly. "Funny and smart and… genuinely nice to everyone she met. She was always smiling, putting on a brave face. And she used to fiddle with my hair, try to flatten it, it was always sticking up in every direction… She loved to read and play the piano and garden. She'd spend hours pulling weeds and making sure all her flowers were in just the right order…" He looked up then, his brow furrowed. "She was going back to college. She wanted a better education so she could start over, support me and my brother without my… my dad there."

Bonnie's thumb stroked across his knuckles gently. "You sound really close."

"We were. She was… one of the best people I ever knew." And she would have been completely horrified with what he had done with his life. He swallowed down the burning swell of emotion in his throat. "What about you? Are you close with your mom?"

"Uh, no." She shook her head, offering a faint, half-smile. "No, she left when I was little, so I grew up with my dad. He was… busy, a lot. But he loved me, he made sure I always knew that. When I was younger, he used to try and make up for my mom's absence. He'd let me do his make-up and he'd sit across from me at my fake tea set and…" She grinned then. "He made up this alter-ego for himself. He was called  _Mrs. Plumberry_ , and he would only ever eat the chocolate macadamia cookies, because those were my least favorite, and he spilled his _fake_ tea every time, and he'd make such a fuss about it…" She shook her head fondly, her eyes distant and sad. "He passed away last year; heart complications… I think it was stress. He always stressed."

"I'm sorry."

"It's okay," she assured. "I'm getting through it."

He eyed her thoughtfully. "Do you ever wonder what it would be like if your mom stayed?"

She nodded slowly. "I have, yeah. I know she has a new husband and a step-son, so… She figured out how to be a mom eventually. She just… wasn't ready to be mine, I guess. But, it's okay. I mean, when I was younger, I wondered a lot. Compared myself to others, wondered why Caroline's mom stayed but mine didn't. Wondered what I  _did_ that made her run. But… I grew up and I realized that her insecurities were her own. Her reasons for doing what she did were  _hers_ , they had nothing to do with me. I was just a kid, I couldn't make her do anything. She made her own choices."

He imagined the same could be said for him and his father. Giuseppe was his own man and he made his own mistakes; many of them. Not the least of which was beating his children and killing his wife. But maybe Bonnie had taken the other path. Maybe instead of embracing that darkness and the cruelty offered by a bad parent, she had decided to focus on the good she had in her life and walk a better path. While he had chosen to stew in his misery and pain, and let it shape him into the man he was now. Which was certainly not someone she should be eating dinner with. Or even speaking to, come to think of it.

Their dinner arrived then, and their attention was diverted to the steaming bowls of pasta placed in front of each of them.

"Enjoy," the waiter told them.

" _Grazie. Sembra delizioso_ ," he replied.

He nodded, smiling. " _Prego_." With a bow, he stepped away from the table to attend to others.

Bonnie raised an eyebrow. "Breaking out different languages, too. Wow, you're really pulling out all the stops."

He snorted, unrolling his fork from the fabric napkin. "Does this mean I have a chance at talking you into dessert?"

"That depends on whether dessert is some of their five-tier chocolate cake, or if you're hoping for a nightcap at my place…"

"Which is more likely?"

She bit her lip. "I haven't decided yet."

He ginned slowly and then reached for the bottle of wine to top them both off. "So, tell me more about yourself… What music do you like, what books are you reading, what do you do on your weekends?"

All of it was information he already knew, he could probably detail it to her better than she could him, but he wanted to hear her tell it. He wanted her to share the little bits of her life with him like he should be privy to them, rather than because he had invited himself into it. And he knew, without a doubt, that what he was doing was walking a very fine line. He was not a friend, not a good person, not worthy of her time or interest. But Damon had always been one to break the rules.

He was fifteen years old when he met Katherine Gilbert. He'd been dating Elena for six days when her siren of a twin walked into the room, all hips and sarcasm and enough self-confidence to fill three rooms. Where Elena was sweet and down to earth, Katherine was fire and manipulation. He looked at her and he saw destruction, and when he looked at Elena, he saw redemption. Damon didn't want to be redeemed. He wanted to burn for what he did, what he  _didn't_ do for his mother. So he let Elena try to lure him onto the right side, let her believe that he was better than all the stories told about him, all the warnings whispered in the halls at school. He let her stand up for him to her father, telling 'daddy' that Damon was different, Damon was good, Damon was  _not_ his reputation. And when she wasn't looking, he flirted with Katherine's sinfully red and pouting lips. He walked closer as she teased and promised and lured him far across that dangerous line of good and bad and acceptable. Some days, he wasn't sure if he was being manipulated or if he was asking her to ruin him. Other days, he didn't want to know.

He did love Elena. He loved who she was and who she thought he could be and even who he wanted to be for her. He loved how she believed in him and hoped for him and how, for very brief moments, he felt like the chains of his mother's death and his father's rejection had been sloughed off. But loving Elena was an unreachable dream, one that he dashed before it had finished growing.

He loved Katherine too. He loved the darkness he saw in her that so resembled his own. He loved her cunning and her honesty in exactly who she was. He loved that she made no apologies and offered no excuses, and she expected the same in return. Katherine was passion and chaos and the eye of a hurricane. She swept him up and spat him out in the same breath, and he enjoyed it far more than most would, or should.

There were a string of women after them, some nameless and forgettable, others that would leave their own little mark to remember them by. But love was left in Mystic Falls, along with the boy he used to be and the brother he promised and lied to. Love was buried with his mother, six feet deep, along with his inability to save her or himself or Stefan. Love was like smoke, coiling through his fingers, ungraspable by blood soaked hands. And truth be told, he hadn't been sure he'd ever wanted to hold it, to fold it between his fingers and let it fill the cracks of his palms. He wasn't sure he was capable of returning love, of being the type of person who  _deserved_ love, and the idea that he might come so close to having it only to be reminded of those very issues always kept him from truly having or enjoying it. He sabotaged himself with Elena, and with Katherine too. There was no hope, no future, for him with either girl. Elena would never forgive him and to Katherine he would always be a tool in her resentment toward her better-liked sister. He was a piece of her chess board just as she was to him. They weren't yin and yang but yang and yang, and that was all they could ever be.

Love became a distant concept. An idea. An imposition. A question rather than an answer. But now he wondered… He watched as Bonnie coiled strings of pasta around the tines of her fork and raised it to her mouth, as her tongue peeked out to swipe away the drop of sauce that lingered on her bottom lip. He watched her fingers wrap around the stem of a fine wine glass and raise it, letting red liquid stain her tongue and slither down her throat. He watched her tuck her hair behind her ear and tug at a silver stud, twisting and turning it absently. And he thought of how she looked on Sundays, all loose curls, sweat and frustration, the determination on her face as she twisted and moved, making the music bend to her will.

She was… exquisite in her humanity. Her normality. Her richly regular existence. She was not a killer, a criminal, a beater of small children and imprisoned wives. She was not a manipulator nor a doe-eyed daddy's girl trying to save the bad boy. She was simply  _Bonnie_. Bonnie who loved red wine and jazz music and yoga in the park. Bonnie who smelled of fresh lilacs and hints of honey. Bonnie who always picked her oranges up at 4:42 every Friday, because she closed her shop doors at exactly 4:30 and it was a twelve minute walk to the store. Bonnie who smiled with her whole face and never just her mouth, whose laughter filled her eyes, and who wrinkled her nose when she disagreed with something, which was often.

"How's yours?" she asked, and he realized he was halfway through his pasta without having tasted one bite of it.

He scooped a bite up with his spoon and popped it into his mouth, stirring his tongue around so the sauce spread and set off his taste buds. He hummed appreciatively, chewing as he told her. "Delicious. Yours?"

"Really good. So, you think you'll try it again?"

"I will. Especially if the company is just as enjoyable."

She licked her lips of stray sauce and raised a curious eyebrow "Are you asking me out to eat again?"

"Only if you call it a date."

She stroked her tongue over her teeth, and raised a shoulder. "I'll decide when this one's over."

"Fair enough." He scooped up another bite before asking, "So, what is your  _'Grams'_ like?"

Humming, Bonnie nodded. "Amazing. And  _smart_. She was a college professor; she taught women's studies for years. She's really passionate about it, and she used to bring her work home all the time, so you can imagine we had a lot of debate and conversations. I wouldn't be half the person I am today without her."

"She sounds pretty interesting."

"Oh, she is. She's retired now, but she still attends a lot of rallies and she gets asked to speak on women's rights and history. She's been doing a lot of traveling lately. She thinks she's going to die soon, so she says she wants to see as much of the world as possible." Bonnie rolled her eyes. "I'm not worried. She's got another ten years left, at least."

"Sounds like a tough one."

"Definitely." She smiled. "So what brought you to New York anyway?" she wondered.

"Work," he answered. "I was in Chicago for a long time, but business was better here, so I moved. What about you? Did you grow up here?"

"No, I grew up in Whitmore County, not far from the college actually. It's in Virginia."

Damon paused. "Whitmore, really?"

"Mmhmm. That's where my Grams taught."

He swallowed tightly. "She taught women's studies."

"Yeah, she was a pretty big deal there. I went to Whitmore for two years before Caroline and I moved down here to New York and started going to NYU."

She was still talking; he could distantly hear her saying something about Caroline becoming a news anchor and how it was her dream career since she was a little girl, but Damon was stuck on the spiral his thoughts were taking.

Bonnie  _Bennett_.

Meaning she could be, and probably was, the granddaughter of Sheila Bennett. The woman his mother had met through college, a professor that was willing to take them in when he was twelve and his mother wanted to start over. His throat tightened. If it had happened, if his mother had gotten away, if he'd  _saved_ her, they would have grown up in Whitmore County. He would have known Bonnie the whole time. She would've grown up underfoot, alongside his brother. They were the same age. His heart hammered in his chest. What if's ran through his head at top speed, tripping him up completely.

"Damon?"

His hearing cleared abruptly and he blinked a few times, focusing in on Bonnie across from him.

She smiled faintly. "You okay? You kind of zoned out on me for a minute there..."

"Yeah, sorry, I'm fine. You were saying something about Caroline and her dream of becoming a news anchor?"

She waved a dismissive hand. "Long story short, her dream came true. She also married the man of her dreams and has a daughter on the way, so, chock one up for life fulfilled."

He hummed. "What about you? No husband or kids I should be worried about?"

Shaking her head, she said, "Almost, once. I had a fiancé back at Whitmore, but…" She screwed up her nose. "He wasn't the one."

He broke his garlic bread in half and took a bite. "How'd you know?"

"He was a good guy. Sweet and nice and funny, but… I don't know. In high school, Caroline was a total boy freak. The cuter the better, her standards weren't all that high, or well, so it seemed. She was kind of insecure and super neurotic. I think she always expected whoever she dated to just… get sick of her eventually. So she tried really hard to pretend like she didn't care and she was okay with a short term boyfriend. Which, there's nothing wrong with that, but… She was always a romantic at heart, and I think she was always waiting for that 'right' guy.

"For me, dating wasn't really a big deal. I was kind of quiet compared to Caroline. She was outgoing and loud and attention getting, and then there was me who was just academic and quiet and always the friend. I don't know if it bothered me. Maybe it did at the time, but now that I look back on it, I'm okay with it. It wasn't really until college when I felt like maybe I was missing out on something. And that was mostly because Caroline went ahead and found her soul mate." She rolled her eyes. "I know, I know, it sounds cheesy. But… if you knew them, they just  _fit_ together. They're best friends and they complement each other. He gets all broody and grumpy and she can pull him out of that headspace with a smile. And she gets all neurotic and crazy and he just…  _looks_ at her, and she takes a breath and calms down. So, you can imagine, when faced with  _that,_ being content with your average relationship was hard…"

She shook her head. "I met Jeremy in my freshman year. He was always bent over his notebook, sketching, and it took me weeks to figure out he was drawing me. It was romantic. I was flattered. So when he asked me if I wanted to go to a party with him, I said yes. I'd dated before, just not a lot, but things with Jeremy happened quickly. It was like I fell in love overnight and, after that, it just grew…. He asked me to marry him a year later and I said yes, at first."

She frowned, eyes narrowed in memory. "But then a month passed and another month and part of me was just so hung up on how happy Caroline was, you know? Like, I looked at her and it was so obvious that she  _knew_. Without a shadow of a doubt, she knew who and what she wanted and she was going to get it. And then I looked at my relationship with Jeremy and, it wasn't that it was lacking, exactly, it just… It wasn't quite what I wanted for myself. I wanted the passion and the perfect fit and I wanted to feel how she did. Like she was… found. Everything she'd looked for and everything she wanted  _found_ her. And I didn't feel like that was Jeremy for me. So, when Care said she was moving to New York, I said I'd go with her, and the rest is history."

"You ever regret it? Not marrying him."

She smiled. "No," she said honestly. "He met someone else. Anna. And they're  _perfect_ for each other. So I don't think he regrets it either. He was mad at first. I guess, for him, maybe he really did think I was  _it_. But then he moved on, he met Anna, and he realized he had no idea what 'it' was." She sipped her wine then, and when she placed the glass back on the table, she wondered, "So? What about you? What awful trials and tribulations in love have you gone through?"

"Ah, well…" He frowned. "My high school dating experience was…  _bad_. And it was almost entirely my fault."

"Ooh, I hear a good story coming on." She filled her mouth with pasta and waved her fork for him to continue.

"Uh, well, my first real girlfriend was Elena. And she was… good. Good person, good daughter, good girlfriend. Pretty much the epitome of perfection."

" _But_ …"

"But my second girlfriend was Katherine, who was pretty much the exact opposite of Elena. Which is funny because she was her twin sister, and I was dating them at the same time."

Bonnie's mouth fell open. " _No_ …"

He winced. "Yeah."

"That's awful!"

"I know, it was terrible. I was a giant jackass."

"You were," she agreed.

He laughed under his breath. "Anyway, I fell for both of them, and I destroyed Elena's heart, and my own in the process."

"What about Katherine?"

"Uh, she was fine, I think. She was never in love with me. She just… really hated her sister. So she looked for every chance to mess with her. And I fit the bill, I guess."

"Wow. That…  _sucks_."

He half-smiled. "Yeah, well, not all of us can be Caroline."

"Amen," she said, raising her wine in cheers, and he tapped his own against hers gently.

They finished their meals while trading idle chit-chat, something Damon had always considered himself too impatient to bother with. But it seemed they shared all the personal information they could handle for one evening, and he rather welcomed a little more levity to the situation.

Just as the waiter came to clear the plates, she stood. "I need to use the ladies' room. I'll be right back."

Folding his napkin up, he said, "Is this the part where you sneak out through the back window and I never see you again?"

She grinned, and with a wink, told him, "I guess you'll have to wait and see."

As she walked away, he watched her, and found himself smiling when she looked back at him over her shoulder. When she was out of sight, he leaned back in his chair and finished off his wine, offering his credit card to pay for their meals. He stared out the window a while, watching strange faces pass by, mid-conversation, unaware of what lurked just beside them. Much as their meal had been a nice break from reality, it inched its way back in, reminding him of all the ways he didn't fit into the picture they'd carved at this table, sitting across from each other, assuming honesty. He was a pretender. A killer. A monster in disguise.

When she returned to the table, he could feel the words heavy on his tongue; an excuse, a lie, a truth. He needed to go, to walk away from her and out of her life. He wasn't sure how he would keep her from being killed. Or would he? He could walk away and leave the job for someone else. A surge of disgust, at himself, swept through him. He'd spent hours talking to her, getting to know her as more than just a target, more than just someone at the other end of his scope. And years from now, on his death bed, she would probably be the only name of any of his victims he dared to remember. Despite everything he knew, everything he'd done, he looked at her and all of his sins seemed secondary.

She was human; strong and frail in equal measure. She was  _somebody_. And he liked her. Liked who she was and what she represented and who she could be with him,  _to_ him.

"So, how about that night cap?" she suggested, staring down at him, an eyebrow curved in question.

And he should have walked away, should have never approached her in the first place, but instead, he stood and he held an elbow out. She tucked her arm through his and he smiled, leading her out of the restaurant.

There were many things Damon could, and should, regret in his life. This was not one of them.

**Notes for the Chapter:**

> This will be 4 to 5 chapters, depending on whether or not i decide to explore stefan and damon's relationship a little more in future. the next chapter is mostly smut and fluff, and then it's back into the action and dealing with the issue of bonnie having a target on her back. this was honestly a lot of fun to work with. i tend to love writing au's, so that shouldn't be a surprise, but i've never been partial to the all-human stuff, which is funny, because my most popular fic is of them as humans, but they still had the magical history there to work off of. this is just straight human. it was interesting to rework their history and dig around in damon's psyche a bit tho. he's a complicated guy, especially here, fighting against who he thinks he is, who he is, and who he wants to be.
> 
> also, for anyone wondering, a new update to " **Til Eternity** ," is on its way, hopefully this weekend, so keep an eye out! :)
> 
> anyway, i hope you enjoyed it! please try to leave a review; they're my lifeblood!
> 
> \- **Lee | Fina**


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